Process for the preparation of reaction products of cycloaliphatic epoxides with multifunctional hydroxy compounds

• US 6,774,250 B1
• Filed: 08/02/2002
• Issued: 08/10/2004
• Est. Priority Date: 06/12/1999
• Status: Expired due to Fees

• Current Assignee: Huntsman Advanced Materials Americas, Inc.
• Original Assignee: Huntsman Advanced Materials Americas, Inc.
• Inventors: Hatton, Kevin B., Rabener, Christiane, Rabener, Claus W., Barker, Pauline G.
• Primary Examiner(s): Trinh, Ba K.
• Application Number:
  US10/018,667
• Time in Patent Office: 739 Days
• Field of Search: 549/546, 549/547, 568/609, 568/619, 568/648, 528/92, 528/110, 528/406, 528/408, 528/410, 528/416, 528/418, 528/421
• US Class Current: 549/546
• CPC Class Codes: C08G 59/24 carbocyclic
• CPC Class Codes: C08G 59/62 Alcohols or phenols
• CPC Class Codes: C08G 59/68 characterised by the catalysts used

Abstract

The invention relates to the process for the preparation of liquid reaction products of cycloaliphatic epoxides with mono- or multifunctional hydroxy compounds. The process comprises reacting a polyfunctional cycloaliphatic epoxy resin with a mono- or multifunctional hydroxy compound in the presence of a heterogeneous surface-active catalyst. The invention also relates to curable compositions containing the product obtained by the process.

Claims

1. A process for the preparation of liquid products, having an epoxide content greater than 0.1 mo/kg, resulting from the reaction of cycloaliphatic epoxides with multifunctional hydroxy compounds which comprises reacting a polyfunctional cycloaliphatic epoxy resin with a multifunctional hydroxy compound in the presence of a heterogeneous surface-active catalyst selected from the group consisting of activated aluminum hydroxide, hydrated aluminum oxide, amorphous silica, activated carbon and cationic ion exchange resins and isolating the reaction product.

2. The process according to claim 1, which comprises reacting a polyfunctional cycloaliphatic epoxy resin selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate and bis (3,4-epoxycyclohexyl methyl) adipate carboxylate.

3. The process according to claim 1, which comprises reacting a multifunctional hydroxy compound selected from the group consisting of pentaerythritol ethoxylate, polyethylene glycol, polytetrahydrofuran, polycaprolactone diol or triol, tripropylene glycol, glycerol propoxylate and dendritic polyols.

4. The process according to claim 1, which comprises reacting the epoxy resin with a multifunctional hydroxy compound in the presence of activated, porous, solid aluminum hydroxide having the general formula Al₂O_(3-x)(OH)_2x where x ranges from about 0 to 0.8.

5. The process according to claim 1, which comprises reacting the epoxy resin with a multifunctional hydroxy compound in the presence of hydrated aluminum oxide selected from the group consisting of crystalline aluminum hydroxide and gelatinous crystalline aluminum hydroxide.

6. The process according to claim 1, which comprises reacting the epoxy resin with a multifunctional hydroxy compound in the presence of amorphous silica selected from the group consisting of silica sols or colloidal silica, silica gels, precipitated silica and pyrogenic or fumed silica.

7. The process according to claim 1, which comprises reacting the epoxy resin with a multifunctional hydroxy compound in the presence of liquid-phase activated carbon in powder, granular or shaped form.

8. The process according to claim 1, which comprises reacting the epoxy resin with a multifunctional hydroxy compound in the presence of macroporous or macroporous crosslinked sulphonated polystyrene or crosslinked polyacrylic cationic ion exchange resins.

9. The process according to claim 1 which comprises reacting at elevated temperature the polyfunctional cycloaliphatic epoxy resin with the multifunctional hydroxy compound in the presence of a heterogeneous surface-active catalyst of claim 1.

10. The process according to claim 1 which comprises cooling the reaction mixture, removing the catalyst, and isolating the reaction product.